Jessica and Tom 04: New Relations

Tom's body jolted as if he were electrocuted and he moaned in ecstacy as the triggered dry orgasm flowed over him. His breathing was fast and gasping as he quivered and shook. Lucy slipped him from her mouth "Wow he really enjoyed that, I could feel his sissy clitty throbbing in my mouth." Another moan escaped him as he slowly came down from his high.

Michelle gently stroked his belly as she reached in to kiss him, "Did you enjoy that sissy?" Tom could only nod as he fought to catch his breath. His ecstasy was short lived however and a pained look soon replaced that of pleasure. "Ah, I see you're starting to cramp, hold onto it a little while longer, it will pass." She gently rubbed his belly and Tom felt the warm sensation of Lucy slipping his still rigid member back between her slick lips creating a confusing feeling of both discomfort and arousal. As quickly as the cramp began it subsided and he relaxed as the urge to expel the fluid waned, he breathed again.

"Excellent," said Michelle, "the next time you feel the cramp I want you to go and expel the fluid" she gently moved his legs from the stirrups and let them hang close to the ground. "Once that's done, Lucy has another new sensation for you to try." He sighed as he felt Lucy withdraw from his cock and she looked up at him grinning widely as she fixed her lipstick.

Sure enough the cramp returned in short order and Tom felt the level of urgency increase so he slipped quickly off the chair and as gracefully as possible tottered across to the bathroom. As soon as he sat the fluid began to flow with far more pressure than he had thought and for far longer.

After a few false finishes Tom felt it safe to return so tidied himself up and exited the toilet "All finished I see, feel all clean inside?" Said Lucy

"Yes Miss Lucy" Tom replied with some trepidation as she had now donned a similar nurses outfit to Michelle but hers was in black with red trimming, 'good nurse, bad nurse' Tom mused as he was beckoned back to the soft leather of the gynae chair.

Michelle clipped his cuffs back onto their anchor points while Lucy secured the straps across his middle and placed his feet in the stirrups once again and secured straps around them too, now totally imobilising him in place. "Tom do you know what a sound is?" Michelle asked quietly in his ear.

"Of Course Miss Michelle, it's a noise like talking or dropping a rock on concrete" he replied naively.

"Not quite what I meant but would you like Lucy to show you?"

Once again his response of "Yes" leapt from his mouth without a thought.

Lucy pulled the covered surgical tray to her side and she stood at his waist. "I've been really looking forward to trying this with you my sweet little agreeable sissy. I've practiced on Jacob and I'm pretty good now" She smiled mischievously as she pulled the cover off the tray to reveal a row of long thin pieces of metal with a slight curve in the end, all neatly arranged from thinnest to fattest.Tom had a bad feeling about what was coming next.

"These are Lucy's sounds but they aren't really noises as you can see" Said Michelle as she picked one up in a gloved finger and showed it to Tom up close. "You see these are used to slip down your sissy clitty and stretch out your pee hole ready for the next bit of fun." Tom filled with fear and his face whitened. "Don't worry, she's really very gentle and its quite a pleasurable experience, so Jacob says." She chuckled then added "You're are sure you want to play with Lucy's sounds aren't you?"

Tom replied immediately "Yes Miss Michelle"

"I thought so."

Tom felt the cold sensation of lube being dabbed on the end of his still rigid cock then the even colder sensation of the steel probe as Lucy held it at the tip of his member. She smiled sweetly but her eyes gave away the desire she felt to exert her control. The tip of the probe slipped slowly into his cock and Lucy continued to support it. "I love this next bit, it just proves you men are just hungry to be filled." With that she let go and Tom watched transfixed as the probe easily slipped all the way down his urethra, stopping only when it got to the flared end.

Lucy took hold of the top of the sound and Tom felt her start to slowly withdraw it then drop it again allowing it to sink deep into him. Tom moaned as it was the only thing he could do as the sensations assaulted him.

"Ooops I think we forgot something Lucy!" Exclaimed Michelle as she held up a flared butt plug with several pipes coming from it.

"Oh I think we did, do you want to do the honours my love?" Michelle grinned and grabbed the bottle of lube then sat on the stool between Tom's open legs. Tom soon felt the cool tip of the plug pressing against his ass before a little more force was used to push the fat plug home.

"That is one hungry little ass young man, just look how easily it gobbled up that plug!" Michelle took hold of the bulb at the end of one of the cables and squeezed it a few times making Tom moan again as the plug inflated within him. Finally she turned the dial on a box on the other cable causing Tom to twitch as vibrations fizzed against his prostate.

Lucy withdrew the first sound and chose a slightly larger one repeating the process of holding the tip at the opening of his dick then allowing it to slowly slip an inch or so in before allowing gravity to slide the heavy sound deep into him. Tom felt his world spinning as he twitched and jerked with each pulsation of the plug and each movement of the sound as Lucy pulled and released the sound.

Then a new sensation bombarded him as Lucy used her lubed hand to start to rub his cock with the sound in place. The solid steel rod filling his urethra presented an unusual and cool feeling and made her touch feel even more sensitive.

Lucy withdrew the sound completely and rubbed his cock with her gloved hand before selecting the next size of sound. This one was larger again and Tom didn't think it would fit but he was a jittering mess at this point and in no position to string a sentence together let alone object.

The large sound once again rested inside his tip being held gently by his tormentor before being released. The thicker girth caused Tom to moan as it stretched him. "Oh yes there it is, that's the one." Lucy exclaimed "do you feel it Tom, pushing against your bladder, making you feel like you need to pee while your prostate gets massaged by the plug. Michelle began to tease him by kissing his shaft from his shaven balls all the way to the tip leaving deep red lipstick marks all the way up his member.

As she got to the top of his shaft she teased him with her tongue on his glans before reading the number from the top of the sound. "Number 10 on the first go is quite impressive. Shall I get the foley?"

"I think so, we don't want to over do things. Lucy smiled sweetly enjoying Tom's involuntary twitching as his senses slowly became overloaded. "Oh look at the precum bubbling past the sound!" She exclaimed swiping it up with her gloved finger and presenting it to Tom's open mouth "Lick!" She commanded and Tom obeyed.

Michelle went to a nearby closet and retrieved a surgical package then returned to her stool between Tom's legs where she laid a green surgical cloth on the tray next to her and laid the package.

A noise was heard at the top of the stairs "Are we having fun down here? May I come down?" Called Jessica.

"Of course, you're just in time for the main event, we're about to take the piss" Lucy said and they both chuckled like school children. The clip clop of her expensive heels heralded Jessicas arrival in the play room.

"Oh my, Tom they are having fun with you aren't they. I do like a good game of doctors and nurses. So what's next ladies?" Jessica peaked over Michelles shoulder and smiled knowingly. "Oh, I see what you mean, I don't think he's going to like that."

"Of course he will, look I'll even ask him." said Lucy. "Tom my sweet little sissy, would you like Miss Michelle to slide a Foley catheter down your cock and take away all your piss?"

"Yes Miss Lucy I would" Tom said through his haze.

"Oh that's a bit mean ladies, I like it! Tom, this might be a little uncomfortable for you."

Michelle opened the plastic package while Lucy slid the metal sound from his cock. Next she applied a blob of lube to the tip of his cock then loosened the valve on the butt plug to allow it to deflate to its original size causing Tom to moan at the feeling of emptiness it left.

With his cock still erect Michelle presented the tip of the catheter to the tip of his cock and applied a little pressure to slip it inside. Then inch by inch she slipped the rubber tube into him until she felt resistance.

"Tom this might be a little uncomfortable but I need you to try to pee for me so we can open your bladder and get the catheter in." She once again applied pressure and soon felt the tube move past the sphincter in his bladder. "Good boy, there, almost done." She noted the flow of his pee down the tube into the attached bag and turned the small spigot to stop the flow. Finally she used a small bulb to inflate the balloon inside him to keep the tube in place.

"Excellent. Now we control your pee completely. I can open this tap and let it flow out into this bag, or I can turn the tap off and leaving you desperate to pee and unable to do so. What fun!" She turned the tap and allowed the pee to flow once again and enjoyed the look of relief on Tom's face as his bladder emptied. "Hmm 600ml, seems normal" she said as the flow subsided. "Tom sweetie, put it away" with that his cock softened "That never gets old." She mused.

Disconnecting the bag from the tube she attached a large syringe full of clear liquid. "Now for the fun part. You've seen we can take away your pee but we can also put it back." Tom wriggled against the bonds but couldn't free himself as she began to push the plunger and the Tom felt the flow of liquid back into his bladder causing him to yelp in surprise.

"Oh that is very special, I've only seen it done one way when a sub was forced to drink a lot of water then had the flow played with over several hours. The poor thing was in agony" Jessica said as she watch Tom squirm at the odd sensation of fluid being put back into him. After two large syringes had been squeezed back into him Tom was feeling desperate to pee but, as promised, no longer had control of that particular function.

"Miss Michelle I need to pee, please let me pee" he whimpered

"No not yet, I think I want to see you squirm a bit more and she pumped up the plug in his ass once again, adding pressure to his bladder. Tom strained against the bonds that held him firmly in the exam chair.

"So I think I've made progress with Jacob, I have him drifting into trance easily now and I have inserted his suggestion not to cum without permission just like poor Tom here." She glanced over at Tom and enjoyed seeing him struggling and keening at the full sensation he was feeling. Michelle took pity on him and pulled the plunger removing 100ml of fluid from him but still leaving him in some discomfort.

"That sounds wonderful!" Lucy replied "Can we add some other triggers?"

"We can but only simple ones at this stage, I don't want to be too ambitious and have them not take properly. What would you like?"

"Umm, how about not touching his penis unless peeing or if given permission?"

"I think we can arrange that. I'll pop back upstairs and do that while you deal with poor Tom here." And with that Jessica clicked her way back up the stairs.

"I think from here on we should perhaps do one syringe per orgasm, does that sound fair Tom?" Michelle said.

He didn't need the suggestions of saying yes to agree, the desperation to pee was enough for him to agree to anything "Yes Miss Michelle" he gasped. Lucy pressed the recline on the chair till he was laid flat with his legs still in the stirrups. Slipping her nurses skirt up to reveal her shaven snatch she lowered herself onto Tom's face and allowed his tongue to find its way to her clit.

"I've heard your are good little pussy licker Tom so don't let me down" Lucy said as she ground her pussy onto his face. His eager tongue was on the spot in moments and Lucy was soon moaning with delight as her clit was sucked and licked. Her breathing quickened and her moaning became cries as her orgasm approached.

She reached down and used her fingers to open her vulva so she could watch Tom's rampant tongue flit about her pussy allowing him to target her clit more accurately. "Lick that pussy you dirty little sissy, make me cum or you're pee will stay right where it is." She ground her hips harder and harder as her climax approached before shaking and screaming with delight as it overcame her and she came hard on Tom's ruined face.

Michelle withdrew the plunger as Lucy dismounted him and then replaced the syringe with a fresh bag and kept the tap closed. She lowered the chair slightly and kissed him passionately, his face slick with Lucy's juices. "Mmm I love tasting my lover." She said as she straddled his head and lowered her own wet pussy onto his waiting face.

Michelle was very aroused, she loved the control she had over men, her moaning began almost the instant Tom's tongue entered her. Lucy, standing beside her horny lover kissed her passionately while she slipped her hand to her own snatch to sneak a second climax. Tom was as diligent as before and made sure every flick of his tongue over her clit was of the highest quality. In a few minutes Michelle was moaning heavily and her pussy was slick with her own arousal. Her legs began the telltale quiver of orgasm. Tom felt her grind become more purposeful and her moans transition to screams of pleasure as Lucy joined her in a mutual orgasm. Michelle's slit gushed fluid into Tom's waiting mouth as she came hard, jerking and spasming in delight at her peak.

"Do like my cum running over you and ruining your makeup sissy?" She said in a husky gasp as she looked down at Tom's now very ruined face.

"Yes Miss Michelle, I love your cum and live to serve." He replied catching his breath from being smothered for what seemed like the longest time. The answer was genuine, he really did love licking pussy and the fact that she had squirted all over him was a testament to a fully enjoyed orgasm.

Michelle dismounted and went to his waist area. Tom felt the sweet release as she opened the tap on the catheter and the fluid once again drained from his bladder into the waiting bag. Once the flow stopped she took his cock in her thumb and forefinger and held it up to Lucy's waiting hand. Without warning she pulled gently and Tom moaned at the odd sensation as the catheter withdrew from deep within him.

"Now pop to the bathroom and fix your face, we're not quite done with you yet" Lucy said wide eyed after her second cumming. Tom was released from the chair and he took his clutch bag with him to the toilet to try to rescue some of his makeup.

***

Another knock and the familiar click of heels on the stairs announced Jessicas second entrance but this time she had Jacob in tow. He padded softly behind her in bare feet, led by the leash and collar round his neck. His cock was exposed, rock hard and slick with Jessicas womanhood. Her rosy complexion gave her away "I may have had a test drive, just to make sure everything had taken." She said coyly. "He really does have a marvelous cock."

"And did he... perform to your desires?" Said Lucy

"Oh yes, his balls are still full and unsated, he's really very very horny now, if he was able I suspect he'd be trying to rub one out right now."

Tom returned from the bathroom, his makeup repair job was commendable considering the state it had been when he had been dismissed. His lips back to a deep red and only a hint of smeared mascara gave away the fun that had been had.

He was guided to the large white bed in the centre of the room and laid in place by Michelle. "I think a competition is in order, just like at the retreat. Whichever lady cums first wins, whichever slave cums first loses. If it's a tie, the slave who didn't satisfy his lady loses. How does that work?"

"I think that's a wonderful idea, I'll be umpire since I have just ridden myself to a rather wonderful orgasm, so I guess that means you two are the riders?" Jessica replied guiding Jacob onto the other end of the bed, interweaving their legs so that the two girls could fuck facing each other, using the men only for their hard cocks, as it should be. Once the boys were arranged she took a seat at the end of the bed next to Tom and kissing him tenderly. "You look a little out of breath sweetie, have you been busy?"

"Yes Miss Jessica, very, but I think I have performed well"

"I don't doubt that for a second, you are such a good pussy licker and looking at these two wonderful ladies it looks like they have had at least one good orgasm each." She looked at the couple who were looking hungrily at the two cocks on the bed waiting for them. "Looks like Lucy may have indulged more than once." Which elicited a naughty smile from the dark haired beauty as they both unzipped their tight dresses and let them fall to the floor.

Lucy wore a black satin corset which held her curvy figure in a classic hourglass shape. Her glossy legs adorned by expensive black Woolford stockings held in place by ornate garters with cute little ribbons on the clips. Michelle was similar but in a classic red wine satin and black lace corset, her smooth legs also encased in Woolfords but in a glossy nude tone and held up with thick 50's style garters.

Lucy chose Tom before Michelle had the chance, moving to his side of the bed "Thank you so much for the loan of your perfect little sissy, he is such a work of art." She leant in to kiss Jessica and was rewarded with a deep and passionate twisting of tongues before she broke it and said the magic words "Tom my sweet, I think you should rise the occasion."

Tom's flaccid manhood was awake in a moment and quickly hardened at the use of his trigger. "That just never gets old." She said as she slipped the tip of him into her hungry cunt, holding it just at the entrance while Michelle slid Jacob into her own wet snatch.

"Ready ladies?" Jessica caught the anticipation as both ladies bit their lips in excitement as they nodded. "Ready, set..... fuck!"

Both ladies plunged their wet holes onto their corresponding hard cocks, both submissives gasping as they enjoyed the warm embrace of the dominants hot sex. Michelle grabbed Lucy to her and kissed her deeply as they found their rhythm together. Hands wandered as they explored each other with seasoned expertise. Fingers soon finding their way to each other clits for added stimulation. Jessica felt her own cunt throb and slipped her finger in to begin getting herself off at the wonderful orgy before her. Knowing neither submissive could orgasm without their unique trigger made the sight even more arousing.

Breathy gasps, smeared lipstick, inquisitive fingers and building moans were all the ingredients needed to have all three women well on their way to a mind bending orgasm. Both subs ground in the same rhythm aiming for the deepest penetration they could. Jessica could see the dripping slits covering both wonderful cocks with sweet juices as they slipped in and out of the lucky ladies.

Michelle was first to start to arch her back and moan gutturally. Jacob's monster had found the perfect angle and was hitting her G-spot with precision. She began to twitch and shake as her orgasm reached its peak. She cried out as she tipped over the edge and her warm cum gushed onto the raging cock below.

"Looks like we have a winner." Jessica gasped as her own orgasm approached.

Lucy was next to climax. Her moans were primal as she ground against Tom's cock and quivered in triumph as she peaked. Her cunt squirted her pussy juice down the obedient cock below as she squeezed every last drop of pleasure from her clit. Jessica followed moments after, rubbing her own clit to that moment of no return, crying out in pleasure as she crested into orgasm.